Ammonia → HCID 21504103, compound

HRID 1288213Notes

Reaction equation

HRID 1288213 reaction equation
[CH3:1][C:2]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:14][CH3:15])[CH:5]=1)=O.P(Cl)(Cl)(Cl)(Cl)Cl.[NH2-].[Na+].N>C1COCC1.CCOCC.O>[C:2]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:14][CH3:15])[CH:5]=1)#[CH:1]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 24533Sodium amideHCID 24819Phosphorus pentachlorideHCID 137216261-(5-Methoxynaphthalen-2-yl)ethan-1-one

Product 1

HCID 21504103HCID 21504103, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl (5-methoxynaphth-2-yl)ketone (0.25 moles) and phosphorus pentachloride (0.31 moles) are placed in a 3-neck flask equipped with a mechanical stirrer, a condenser connected to a nitrogen inlet, and a thermometer. The mixture is stirred at 33°-35° C for 3 days. The cooled reaction mixture is poured onto 800 g of ice and extracted with 3 × 500 ml of ether. The ether fraction is washed with 2 × 100 ml water 4 × 100 ml of 5% sodium hydroxide, 3 × 50 ml water, 2 × 50 ml of saturated saline and dried over sodium sulfate. The ether is removed to give the chlorinated intermediate. The intermediate is dissolved in anhydrous THF (200 ml) and is added dropwise to a freshly prepared solution of sodamide in liquid ammonia, using a dry-ice condenser. The reaction mixture is allowed to stir at room temperature overnight; then, it is poured into 50 ml of water and 500 ml of ether. The ether fraction is washed with 3 × 50 ml water and solvent gives a residue which is distilled to give 2-ethynyl-5-methoxynaphthalene.

Workup

  1. customequipped with a mechanical stirrer, a condenser
  2. customconnected to a nitrogen inlet
  3. customThe cooled reaction mixture
  4. extractionextracted with 3 × 500 ml of ether
  5. washThe ether fraction is washed with 2 × 100 ml water 4 × 100 ml of 5% sodium hydroxide, 3 × 50 ml water, 2 × 50 ml of saturated saline
  6. dry with materialdried over sodium sulfate
  7. customThe ether is removed
  8. customto give the chlorinated intermediate
  9. stirringto stir at room temperature overnight
  10. washThe ether fraction is washed with 3 × 50 ml water and solvent
  11. customgives a residue which
  12. distillationis distilled

Sources & evidence

ORD record
ord-b9dd3d04b3b542d190a87ca5874d3e42
Source dataset
uspto-grants-1976_10
Patent number
US03987116

Reaction notes

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